


The Assassin and the Hitman

by LoveStiles



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Assassin - Freeform, Assassin Stiles Stilinski, Bottom Jackson Whittemore, Daddy Kink, Hit Man Jackson Whittemore, Jackson is snarky and rude, Killing, Love, Loving Sex, M/M, Minor Character Death, Mob hit, Oral Sex, Possessive Behavior, Sex, Stackson - Freeform, Stiles is bossy and controlling, Top Stiles Stilinski, and Jackson loves it, and Stiles doesn't like it, fluff at the end, hitman - Freeform, killers
Language: English
Status: Completed
Published: 2019-10-29
Updated: 2019-10-29
Packaged: 2021-01-06 06:23:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,101
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21222026
Author URL: https://archiveofourown.org/users/LoveStiles/pseuds/LoveStiles
Summary: Stiles Stilinski is an assassin. An independent hired killer. Jackson Whittemore is a hitman. A mob killer. He works for the gangster Duke Deucalion. Jackson is snarky and rude. And Stiles doesn't like it. Stiles is bossy and controlling. And Jackson loves it. And they're both possessive. There is killing in this story. And hot explicit sex. And love. And fluff. So grab the rail, possums, and hold on for the ride.





	The Assassin and the Hitman

**Author's Note:**

> In this story Stiles is 28 and Jackson is 20.

It was 11 P.M. as Stiles Stilinski parked his car and walked down the street to the bar that he knew about. He had grown up near Sacramento and had done a contract there once. A contract on a very nasty drug dealer. He got to the bar and walked in. It was a smoky little joint, frequented by gay men, drag queens, and their friends. It was Saturday night and the bar was crowded. The dance floor held a few couples dancing, and there were other people sitting at the bar and at tables scattered around the place. Stiles saw the person that the was looking for sitting at the bar. He walked over and stood next to him.  
"Hi, I'm Stiles", he said.  
"I'm Jackson", the young man replied.  
They shook hands and smiled at each other.  
"Buy you a drink?", Stiles asked.  
"Sure", Jackson replied.  
They looked at each other heatedly as they had their drink.  
"Having a good time?", Stiles asked.  
"It's ok", Jackson replied.  
"Just ok?", Stiles asked.  
"Yeah, just ok", Jackson said. "But things are improving".  
They both grinned.  
"Want to dance?", Stiles asked.  
"Yeah", Jackson replied.  
They went to the dance floor and started to dance. The D.J. played a slow number, and Stiles held Jackson close to his chest. He rubbed his hands on Jackson's hips and back.  
"You're being awfully handsy for a stranger", Jackson said. "I should kick your ass for being so forward".  
"Don't be rude", Stiles said in a stern voice. "Talk nice to me".  
Jackson snorted, but he didn't complain again.  
They finished the dance and stood looking at each other.  
"You want to leave with me?", Stiles asked.  
"Yeah", Jackson replied.  
They walked down the street to Stiles car.  
"Wow!", Jackson said. "A Ferrari! You must have some serious dough!"  
"I do alright", Stiles replied.  
They got in the car and looked at each other.  
"I want to take you back to my place and fuck your brains out", Stiles said. "Is that ok with you?"  
"Oh, yeah", Jackson replied. "I'm all for that".  
"But first", Stiles said, "I want you to do a favor for me. And I'll return the favor".  
"Tell me what the favor is", Jackson replied, "and I'll tell you if I can do it".  
"OK", Stiles said. "Don't freak out. I know who you are. And I know that you work for Duke Deucalion".  
"Are you a cop or something?", Jackson asked.  
Stiles chuckled.  
"I'm far from a cop", he said. "I'm actually in the same line of work as you are. You're a mob hitman. And I'm a professional assassin".  
Jackson looked skeptically at Stiles.  
"I haven't heard of an assassin named Stiles", he said.  
"That's because I don't work under my real name", Stiles replied. "Perhaps you've familiar with my professional name. I call myself Red Wolf".  
"Red Wolf!", Jackson exclaimed. "You're Red Wolf? The most famous assassin in the country?"  
"Yeah", Stiles replied. "And I know all about you. Your name is Jackson Whittemore. You're twenty years old. You don't have a boyfriend. You're a hitman for Deucalion. And you hate his guts. You want to be free of him, but he's got you in an iron grip".  
"How do you know all that?" Jackson asked.  
"My specialty is research", Stiles replied. "All my life I've researched and dug up facts on people and places. And when I accept a contract on someone, I research the hell out of them. For instance, I know that you don't have a gun on you".  
"How do you know that?". Jackson asked.  
Stiles grinned.  
"Remember when I got handsy with you on the dance floor?", he said. "I was frisking you to see if you had a gun".  
"I see", Jackson replied. "You're always prepared. Like a fucking boy scout".  
"Don't be a smartass", Stiles said. "I don't like rude people".  
"Ok, wise guy", Jackson said sarcastically. "I didn't take my gun with me because I didn't think that I would need it at the club".  
"You should always have your gun with you, kid", Stiles replied. "You never know when you'll need it. And stop being rude to me. I'm not nice to people who are rude to me. I'm warning you!"  
"Ok", Jackson said. "I get the message. I'll be a polite boy".  
"That's better", Stiles replied.  
He reached across the seat and pulled Jackson toward him. He gave him an open mouthed, passionate kiss. Then he pulled back and left Jackson wide eyed and panting.  
"See how nice I can be when you're polite to me?", Stiles said.  
Jackson caught his breath.  
"Ok", he said. "What are the favors that you want to trade?"

"As I said, I know that you're unhappy working for Deucalion", Stiles replied. "And that you want to be free of him. I'll get you your freedom. If you will lead me to Deucalion's secret hideout".  
"I see", Jackson said. "You have a contract to kill Deucalion".  
'That I do", Stiles replied.  
"A contract from Peter Hale", Jackson said. "He's angry with Deucalion because Duke is moving in on his territory".  
"Bingo. You win the prize", Stiles replied. "You're smarter than I thought you were".  
"So you couldn't find out where the hideout was?" Jackson asked.  
"I couldn't", Stiles replied. "It's too well hidden. Only Duke and three of his henchmen know where it is. And you're one of the three".  
"And the other two are?", Jackson asked with a grin.  
"Theo Raeken and Matt Daehler", Stiles replied.  
"You're good", Jackson said. "Very good".  
"He's there alone with them now", Stiles said. "And I can get them all if I just know where the hideout is. Once they're dead, you'll be free".  
Jackson looked at Stiles.  
"Ok", he said. "I agree to the deal. I'll take you there. I want to be free of the bastard".

Stiles started the car and Jackson directed him to the location of the secret hideout. They drove to a wooded area, then turned off the main highway onto a winding gravel road.  
"How much further?", Stiles asked.  
"About 300 feet", Jackson replied.  
Stiles dimmed the headlights. When he saw the cabin ahead, he stopped the car. Stiles put on a pair of thin lightweight gloves. Then he reached inside his jacket and pulled a gun out of his holster. He attached a silencer to it. He got out of the car, then motioned Jackson to get out.  
"We're going in", Stiles said. "I'll be right behind you. Not that I don't trust you, but don't try anything funny. Or you will end up very dead".  
They walked up the steps to the door.  
"Do you have a key?", Stiles whispered.  
"No", Jackson whispered back. "You have to knock".  
Stiles pulled out a lock pick and unlocked the door. Then he opened it quietly. He pushed Jackson ahead of him and they walked down a narrow hallway. They entered a room and saw Matt and Theo sitting in chairs watching tv. Matt stood up in surprise.  
"Jackson?", he said.  
Stiles aimed his gun over Jackson's shoulder and shot Matt between the eyes. As he fell dead, Theo stood up. He went for his gun, but before he could pull it out of his holster, Stiles shot him between the eyes and killed him.  
Jackson pointed to a door across the room.  
"Deucalion", he whispered.  
They walked to the door and Stiles opened it quietly. They saw Deucalion sitting at his desk. He had headsets on and was listening to music. Suddenly he looked up. He opened the drawer to get his gun and rose from the desk. Before he could pull the trigger, Stiles shot him, also between the eyes. He fell dead on the floor.  
"Wow!", Jackson said. "You're good!"  
"We had better get out of here", Stiles said. "Get your stuff".  
Jackson got his clothes and guns and put them in a backpack.  
They went back to the car.  
"Throw your stuff in the trunk", Stiles said.  
Jackson put his backpack in the trunk of Stiles' Ferrari and they drove back to the highway.

"I can take you where you want to go and drop you off there", Stiles said. "Or I can take you back to my place in L.A. Your choice".  
"Your place in L.A.", Jackson replied.  
"Ok", Stiles said. "And when we get there I'm going to fuck you until you don't know your own name".  
Jackson grinned.  
"That sounds good to me", he said.

"Tell me more about you", Stiles said. "Your early life".  
"Well, my dad was in the army", Jackson replied. "We moved around a lot. There were a lot of kids. Ten kids, to be exact. There wasn't much money. But at an early age I learned to shoot and became an excellent marksman. When I was eighteen my dad told me that I was grown and on my own, and they kicked me out. Then I became a mob hitman for Deucalion. End of story. What about your early life?"

"Believe it or not, my dad is a sheriff", Stiles said.  
"Seriously?", Jackson replied. "Wow!"  
"Yeah, he is", Stiles said. "He's the sheriff in my hometown of Beacon Hills. I grew up there. My mom died when I was ten, so growing up it was just my dad and me. I learned to shoot at an early age as well and became an outstanding marksman. When I was eighteen I left home and became a professional assassin. I work independently, and get contracts to kill. Mostly mob hits, from powerful people. But I also work for the government. Like killing drug dealers in South America. I earn five million dollars from every hit that I make. I'm the best assassin in the country, and my lucrative contracts have made me very wealthy".  
"So that's how you can afford this car", Jackson said.  
"Yeah, that and my high rise condo in L.A.", Stiles replied.

A few miles down the highway they were stopped by a police roadblock and Jackson panicked.  
"Just calm down and chill", Stiles said. "I've got it under control".  
He rolled down his window as a highway patrolman approached the car.  
"How may I help you, officer?", Stiles asked politely.  
"Stiles!", the cop said. "I thought that might be your car".  
"Hi, Jordan", Stiles replied. "What's happening?"  
"A bank robbery in Centerville", Jordan said. "We're stopping vehicles to see if we can catch the robbers. You're out late. Work as usual?"  
"Yeah", Stiles replied. "My hours are unpredictable".  
"Well take care, Stiles", Jordan said. "See you in Beacon Hills at Christmas".  
"Thanks, Jordan", Stiles replied. "See you then".  
Stiles drove off with Jackson staring at him in complete surprise.  
Stiles grinned.  
"Jordan's an old friend from my hometown", Stiles said. "My dad has cleared me with all of the police and sheriff forces in the state. They may suspect what I do for a living, but they don't ask any questions. After all, I do specialize in getting rid of bad guys, and they are ok with that".  
"Wow!", Jackson said. "You are one cool dude!"

They arrived in L.A. a few hours later. Stiles parked his car in the building garage. They got their things out of the car, then took the elevator to the twentieth floor. When Jackson saw Stiles' condo, with the plate glass windows showing the lights of the city shining below and expensive furnishings in all the rooms, his jaw dropped open again.  
"Gee!", he said. "This is the gold standard! You live well!"  
"I like a bit of luxury", Stiles replied. "And I can afford it".

Stiles backed Jackson up against the wall and kissed him passionately. He rubbed his big cock through his slacks.  
"Is this what you want, baby", he asked Jackson.  
"Yes", Jackson replied. "I want you to fuck me".  
"Ok", Stiles said. "But remember, I'm in charge".  
"I'll remember", Jackson replied.  
Stiles grinned  
"And I believe in being considerate to each other", Stiles said. "Especially in the bedroom. If you're not being considerate to me, I'm not happy.  
I don't like rude people".  
He stroked Jackson's hair.  
"I do like a little bit of rough sex, however", Stiles added.  
"So do I", Jackson replied.  
"Then we should get along just fine", Stiles said.  
He looked at Jackson.  
"Bedroom. Now", he said.  
"Yes, Stiles", Jackson replied.  
Stiles took Jackson's hand and led him into the bedroom. He pulled the comforter off the bed and pulled the top sheet down.  
"Strip", Stiles said. "Then get on the bed".  
"Yes, Stiles", Jackson replied.  
Jackson stripped and laid naked on the bed. His body was toned and tight. He had cute little nipples and an eight inch cock and big balls. He had a light dusting of hair on his chest and a thin treasure trail that led down to his thick curly pubes.  
"Beautiful!", Stiles said.  
"Thank you, Stiles", Jackson replied. He blushed.  
Then Stiles stripped. His long, lean body was also toned and tight. He had a massive twelve inch cock and huge balls. He had thick hair on his chest and a wide treasure trail that fanned down to his thick curly pubes.  
"Gorgeous!", Jackson said.  
"Thank you, Jackson", Stiles replied.  
Jackson and Stiles were both aroused. Their big cocks were standing up on their stomachs, hard, red, and throbbing.  
Stiles got into bed and kissed Jackson. Their tongues explored each other's mouths until both of them had to come up for air.  
Then Stiles kissed, licked, and lightly bit Jackson's cute little nipples until Jackson moaned. Then Jackson, kissed, licked, and bit Stiles' large nipples until he moaned as well.  
Stiles licked and sucked Jackson's balls. Then he licked and sucked his hard cock. Jackson licked and sucked Stiles' big balls and huge cock. Then Stiles turned their bodies so that they could lick and suck each other.  
Stiles pulled off of Jackson's cock and looked up at him.  
"Time to fuck you, baby", he said.  
"Yes, Stiles! Please!" Jackson replied.  
Stiles grinned.  
"Nice and polite", he said. "Just what I like!"  
He kissed Jackson.  
"Lie on your back, baby", Stiles said. "And open those pretty legs wide for me".  
Jackson blushed.  
"I'm pretty?", he asked shyly.  
"Oh, baby, you are so pretty", Stiles said, "In fact, you're fucking beautiful!"  
"Thank you, Stiles", Jackson said.  
"You're welcome, baby", Stiles replied.  
"And you're handsome", Jackson said.  
"Thank you, baby", Stiles said.  
"You're welcome, Stiles", Jackson replied.  
Stiles got the lube from his bedside drawer.  
"I'm gonna open you up, now baby", he said. "Because I'm so big, and I don't want to hurt you".  
Stiles looked at Jackson's little pink hole.  
"Sexy", he breathed.  
He lubed his fingers and inserted one into Jackson.  
Jackson moaned with pleasure.  
"Tight!", Stiles said.  
He inserted a second finger, then a third. Finally a fourth finger. He found Jackson's prostate and rubbed his fingers against it.  
""Stiles! Yes!", Jackson said. "Yes!"  
After Stiles finished lubing Jackson's tight hole, he lubed his hard cock.  
"Ready for my big hard cock, baby?" he asked.  
"Oh, yes!" Jackson replied. "Fuck me, Stiles! Fuck me, my love!"  
Stiles put the blunt head of his huge hard cock against Jackson's little hole and pushed it in slowly.  
"Ok so far, baby?", he asked.  
"Yeah", Jackson breathed.  
Stiles pushed his huge hard cock in inch by inch until he bottomed out.  
Both of them moaned at the onslaught of sensation.  
"So tight and hot!", Stiles said. "I can feel you rippling up and down my cock!"  
"So long and thick!", Jackson said. "I can feel every throbbing inch of your veiny dick!"  
Stiles began to fuck Jackson slowly with long firm strokes. Then he speeded up and fucked him hard. They both felt the sparks of pleasure running up and down their spines.  
"Fuck me, Stiles!" Jackson moaned. "Fuck me da….."  
"You can say it, baby", Stiles said. "I like it. And I know you want to say it".  
"Fuck me, daddy!", Jackson replied. "Fuck me harder!"  
"I will, little boy", Stiles said. "I will!"  
Stiles jackhammered his hard cock relentlessly into Jackson's little hole.  
"I'm gonna come, daddy!", Jackson said.  
"I'm gonna come, too, little boy!", Stiles replied.

"Stiles!", Jackson shouted as ropes of thick hot come shot out of his cock and covered his chest and stomach.  
"Jackson!", Stiles exclaimed as he shot streams of thick hot come deep up inside of Jackson.  
They both panted and caught their breath. Then Stiles pulled out of Jackson and laid down beside him. They held each other close and kissed.  
"That was wonderful!", Jackson said. "No one has ever made me feel that way before".  
"It was wonderful for me as well", Stiles replied. "No one has ever made me feel that way before".  
Stiles got a warm washcloth and towel from the en suite bathroom and cleaned both of them up.  
Then they lay in each other's arms and talked.  
"Jackson, baby", Stiles said, "Would you like to join me as my partner in the business? I hear that you're pretty good".  
"I'm not as good as you, but I'm pretty good", Jackson replied.  
"I can train you to be better", Stiles said.  
"I'd like that", Jackson replied.  
"So will you be my partner?", Stiles asked.  
"Yes, my love", Jackson replied.  
Stiles looked into Jackson's eyes.  
"And will you be my mate, beautiful boy?", he asked.  
"Yes, handsome man", Jackson replied.  
They smiled. And kissed again.  
"Sweetheart", Stiles murmured.  
"Darling", Jackson murmured in reply.  
"Happy, baby?", Stiles asked.  
"Yes, my love", Jackson replied.  
"You're mine", Stiles said. "You belong to me".  
"Yes, daddy", Jackson replied.  
"And you're mine", Jackson said. "You belong to me".  
"Yes, baby", Stiles replied.  
They grinned at each other.  
"Ready for another round, little boy?", Stiles asked.  
"Yes, daddy", Jackson replied.  
Stiles slipped his big hard cock back into Jackson's tight little hole and they both moaned in ecstasy.

In the next few months, Stiles trained Jackson to be a better assassin. He became Stiles' partner in the business. He called himself the Blue Fox. He was Stiles' right hand man, and together they became a formidable team.

And every day and every night they make love.  
"Goodnight, Stiles", Jackson says. "Goodnight, daddy".  
"Goodnight, Jackson", Stiles replies. "Goodnight, little boy".  
They kiss and hold each other close, naked in their warm bed.  
"I love you, sweetheart", Stiles says.  
"I love you, darling", Jackson replies.  
Then they fall into a peaceful sleep, holding each other close all night long.

**Author's Note:**

> I hope that you enjoyed my story.
> 
> LoveStiles (James S. MC.)


End file.
